Dyestuffs of the anthraquinone series and process of making same.



EDUARZD nnrr, or rnannronrr-onrnn nam, AND nononr unseen-ore ROEB'IER, OF H6CHST-ON THE-MAIN, GER-MANY, ASSIGNORS TO FfiRI-E'th .tultilii VGEBL MEISTER L'UCIlJS 8c BRllNTING, 9F HCCHSTON-THE-MAIN, GERMANY, It. CGEFEORA- SCION 0'5 GERMANY.

DYESTUFFS OF THE ANTHBAQUINONE SERIES AITD fROCES S OF Evita KING FSAIHE.

and (2 and 3) Hochst-on-the-ltllain, Germany,

respectively,-have invented certain new and useful Improvements in Dyestuffs of the Anthraquinone Series and Processes oil-Making Same, of'which the following is a specification,

' Our invention relates to the manufacture of a new class of dyestuffs dyeing in the vat pure yellow to orange tints, produced by causlng an 0X1d1z1ng'agent to act upon the Specification of Letters Patent.

-(see Bohn,

Application filed {)ctober 26, 1911. Serial No. 656,992.

oz-trianthrimids ow-(li-moanthriminoanthrw quinones) or their derivatives with an alkaline condensing agent, such, for instance, as an alkali, sodium a'mid, sodium amylate, or with a metallic chiorid, such, ior instance, as aluminium chlorid.

The simplest body of the series is regarded as having the constitution of a dianthrm quinonylindant-hrene, and results from the combination of 2 molecular proportions of eardianthrimid with elimination of 2 mole cules of hydrogen; the reaction is therefore similar in every respect to that by which the indanthrene'is produced by ins-ates, of i2 molecular proportions of a-aminoanthraquinone Bem'chte, vol. 43, 999,

products formed by treating the a-dianthri- 1910) mids (a-dlanthraqulnonyllnnds) or the co co ll rot l l l i \/\\\/\/\NH no 00 NH o0 EN a l l a aminoanthraquinone. Indanthrene.

0 00 I 1- w a I 1 l N-C 4H Oz co NH(C14H1Oz) c0 1 oo C14 10z l a a-d'ianthrimid.

The new dyestuffs may generally be rerarded as perazines of the anthraquinone series. (See WVieland,-Be1"iq;tte, vol. 41, page 3484:.) \Vhen dry, they form yellow to dark-brown powders which are entirely insoluble in alkalis and diluted acids, and, with the exception of the derivative of the aoz-diantln'imid,also entirely insoluble in solvents of a high b0ilingp0int. Their solution in concentrated sulfuric acid assumes a claret-red to violet color. They dissolve in Dianthraquinonylindanthrone.

the hydrosultites in presence of alkalis, yielding red solutions which dye cotton yellow to orange shades which are very fast to light and resist very well the action of chlorin or alkalis. The dyeing is advantageously done at ordinary temperature. The simplest bodies of the series are particularly distinguished from the original products by the purity of their tint; thus the ouz-dianlhraquinonylindanthrene is a pure yellow (lyestuft, whereas for instance the product ohi sublimes.

tained by direct action of aluminium chlorid upon owz-dianthrimid yields on cotton, ac cording to British Patent No. 12921 of 1910, brownish-olive tints.

In carryingout our new process we can employ a great number of oxidizing agents, such, for instance, as chromic acid or hypochlorites, the latter having generally given the best results.

For manufacturing the new dyestuffs, We can for instance, proceed as follows:

Example I: 10 kilos of the dyestufi' obtained by heating the ozcz-dianthrimid. with an alkaline condensing agent or a metallic chlorid are treated at about 80 (1, in the form of a 10-20 paste, with 200-300 liters of a solution of sodium hypochlorite containing 6.5% of active, chlorin, until the paste, which is at first dark, does no longer change its color. The dyestuff is then filtered and Washed with water. WVhen dry, it forms a yellow powder, which dissolves in concentrated sulfuric acid with a claretred color, and which dyes cotton from a red vat very fast yellow tint.s.- It is very ditficultly solublev in indifferent solvents, even when heated to boiling, and crystallizes in about 1200 times its weight of boiling nitrobenzene, or in boiling quinolin, in which it is scarcely more readily soluble, forming small orange-yellow entangled needles. hen heated alone, it decomposes only at a very high temperature and partly \Vhen heated with zinc dust it forms a well-characterized compound. The analysis of the dyestutf has given results which are well in accordance with the for mula 'C,,,,II. ,,,N O,.

Example II: The product obtained by the action of aluminium clilorid. or an alkali upon the 1.5di-az-anthriminoanthraquinone (a-trianthrimid) is treated, as above stated, by sodium hypochlorite. The paste, which is at first blackish, gradually becomes more and more red according as the quantity of the oxidizing agent is increased. The operation is considered to 'be complete when the desired tint is obtained.

The dyestuff th'us produced fornis, when dry, a reddish-brown powder; it dissolves to a violet solution in'concentrated sulfuric acid, thus yielding a solution from which it is precipitated in the form of orange-yellow flakes by the addition of. water. It

dyes cotton from a red vat orange-yellow sulting from the condensation of ao -anthrimino compounds, obtained from an oz-aminoanthraquinone compound and an a-chloranthraquinone compound.

2. The process of producing a new anthraquinone dyestuif, which consists in treating with hypochlorites the product olotained by condensing aa-dianthrimid.

3. As new products, the herein-described new dyestuffs, obtainable by treating with oxidizing agents the products resulting from the condensation of aoa-anthrimino compounds obtained from an'oc-aminoanthraquinone compound and an cz-chloranthraquinone compound, which dyestuffs, when dry, are yellow to brownislrred' powders, insoluble in alkalis and in diluted acids and very little soluble in the usual'organic solvents, dyeing cotton from the vat fast yellow to orange shades, substantially'as hereinbefore' described.

4. As a new product, the hereindescribed m dianthraquinonelindanthrene, possessing a constitution agreeing with the formula C H N O which dyestufl is insoluble in water and in diluted acids and alkalis, diflicultly soluble in most organic solvents, soluble in concentrated sulfuric acid, yielding a claret-red solution dyeing cotton in the hydrosulfite vat yellow shades which are very fast to the light and resist very well chlorin and alkalis, substantially as hereinbefore described.

In testimony whereof,-we affix our signatures in presence of two witnesses.

\Vitnesses JEAN GRUND, CARL GRUND. 

